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Compound Detail

CHEMBL1201129

DECITABINE
💊 Approved Drug
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💊 Approved Drug
Nc1ncn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201129
Name DECITABINE
Phase Approved
Structure Type MOL
InChI Key XAUDJQYHKZQPEU-KVQBGUIXSA-N
Therapeutic ✓ Yes

Known Names

2'-deoxy-5-azacytidine DAC Dacogen Decitabina Decitabine Decitabine component of astx-727 Decitabine component of astx727 Decitabine component of inqovi NSC-127716
4
Targets
11
Activities
2
Assay Types
6
PK Parameters
20
Publications
9
Known Names
20
Indications
3
Mechanisms

Molecular Properties

228.2
MW (Da)
-2.14
ALogP
8
HBA
3
HBD
123.5
PSA (Ų)
0.53
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2006
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -citabine
USAN Year 1989

Extended Properties

Molecular Formula C8H12N4O4
MW 228.21
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness 1.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA (cytosine-5)-methyltransferase 3A inhibitor INHIBITOR DNA (cytosine-5)-methyltransferase 3A ✓ ✓
DNA (cytosine-5)-methyltransferase 1 inhibitor INHIBITOR DNA (cytosine-5)-methyltransferase 1 ✓ ✓
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Anemia Anemia, Refractory, with Excess of Blasts Leukemia, Myeloid Leukemia, Myelomonocytic, Chronic Myelodysplastic Syndromes Neoplasms Neoplasms Graft vs Host Disease Graft vs Host Disease Hematologic Diseases Leukemia Leukemia, Myeloid, Acute Lymphoma, Large B-Cell, Diffuse Lymphoma, T-Cell, Peripheral Lymphoma, T-Cell, Peripheral Myeloproliferative Disorders Myeloproliferative Disorders Purpura, Thrombocytopenic, Idiopathic Thrombocytopenia Adenocarcinoma, Follicular

ATC Classification

L01BC08
decitabine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 10 meas. best 7.52
EC50 1 meas. best 4.02

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA (cytosine-5)-methyltransferase 1
CHEMBL1993
 IC50 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
 IC50 7.3 5.0013 50.0 8
L1210
CHEMBL386
 IC50 6.41 6.41 393.0 1
H4
CHEMBL1075452
 EC50 4.02 4.02 94935.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 130.0 mL.min-1.kg-1 Homo sapiens
CL 130.0 mL.min-1.kg-1 Homo sapiens
Fu 1.0 - Homo sapiens
MRT 0.59 hr Homo sapiens
T1/2 0.58 hr Homo sapiens
T1/2 0.1667 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA (cytosine-5)-methyltransferase 1 IC50 = 30.0 nM 7.52 Inhibition of human DNMT1 using polydeoxyinosine polydeoxycytosine DNA as substr... 29953809
Unchecked IC50 = 50.0 nM 7.3 Antiproliferative activity against human EPN8 cells assessed as reduction in cel... 30559935
L1210 IC50 = 393.0 nM 6.41 Compound was tested for its inhibitory activity against L1210 lymphoid leukemia 3806615
Unchecked IC50 = 400.0 nM 6.4 Antiproliferative activity against human BXD-1425EPN cells assessed as reduction... 30559935
Unchecked IC50 = 16149.0 nM 4.79 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 34240.0 nM 4.46 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 41820.0 nM 4.38 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Unchecked IC50 = 55620.0 nM 4.25 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 60390.0 nM 4.22 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Unchecked IC50 = 61300.0 nM 4.21 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
H4 EC50 = 94935.0 nM 4.02 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response HTS to Identify Activato... -

Literature References

PubMed DOI Target Context # Activities
30559935 10.18632/oncotarget.26370 Unchecked 11
27117260 10.1016/j.bmc.2016.03.052 Human immunodeficiency virus 1 7
18426954 10.1124/dmd.108.020479 ADMET 4
28463515 10.1021/acs.jmedchem.7b00176 Unchecked 4
33691794 10.1186/s13148-021-01037-1 A549 4
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
23010273 10.1016/j.bmcl.2012.08.108 Human immunodeficiency virus 1 2
21840716 10.1016/j.bmcl.2011.07.053 Molecular identity unknown 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
19445515 10.1021/jm900403j Homo sapiens 2

Data from ChEMBL 36 via Core Engine